So what I really wanted to find out was if the iPhone was worth the money; and somehow I started down the road of comparison testing. (I guess it really is part of my nature).

I lived with the iPhone on a business trip to San Francisco (talk about bringing the coals to Newcastle) and came back with more questions.

More after the jump.

Some background: I've owned and used several smartphones and PDAs from the major players: Palm Vx, HandSpring Visor, Treo 650 (Palm), Toshiba e750 (PocketPC), Sony Ericsson P900 (Symbian UIQ), Nokia N80 (Symbian S60v3), and my current whip, the T-Mobile MDA (Windows Mobile 5). Heck I even used a Newton MessagePad 2100 back in the day. I own the MDA because I want a phone that can also do data functions, like quick lookups on Wikipedia and do multimedia tasks like playing back video files or MP3s. Native programs like SlingPlayer Mobile and Zagat to Go are gravy. The big annoyances with MDA are the lackluster phone performance, and the smaller 2.5mm headphone jack. I tried using a pair of A2DP Bluetooth headphones, but that didn't work as well as my iPod nano 2G with wired earbuds. The MDA is a middling to fair phone, a great PDA, a passable media player, and a passable Internet tablet.

Now I've also owned several generations of Apple iPod: iPod 2G, iPod 4G (monochrome), and iPod nano 1G and 2G. I used to use a Compaq MMC-based MP3 player before the iPods, and I also own an old Archos av500 for videos on the go.

Now my (current) ultimate pocketable device would give me as many of the following features as possible, and would let me combine the functionality of an iPod and a smartphone:

-A good quality phone, with decent coverage in the NYC area;
-3G or better data;
-WiFi;
-Ability to use iTunes-bought programming and management (Hey, I like being able to check and uncheck content to be synced, even better than the drag-and-drop simplicity of the Archos because sometimes I want to watch things over without having to search for it. Plus iTunes backup is as simple as dragging the iTunes folder over to a shared or USB drive);
-Internet browsing, as close to 'desktop class' as possible;
-Video playback;
-Calendaring with links to Outlook/Entourage;
-Outlook/Entourage Contact management;
-Music playback through high quality third-party earbuds (I like both the Ultimate Ears Triple-Fi 10 Pro and the Shure E4g for quiet room listening or commuting, respectively). This is notable because both pairs of headphones use L-shaped plugs that don't fit in the iPhone;
-Note taking;
-Bluetooth for in-car Handsfree (must have) and dial up networking for laptops (would be nice).;

The MDA plus the iPod nano 2G got me most of the functions above, but I really want a 'one pocket' device, which the iPhone initially promised. Again my scores for the MDA would be: Phone (2.5 out of 5), Internet data tablet (3 out of 5), native apps (5 out of 5), PDA (4.5 out of 5) and media player (3 out of 5). I didn't rate the MDA's email capabilites because our corporate email (still) doesn't support mobile devices aside from a few Blackberries and Goodlink devices.

I borrowed the iPhone for a couple of weeks, with the iPod Touch and an iPod nano 3G as well.

The iPhone was both a revelation and a disappointment. The iPhone was an OK to very good phone, since AT&T's service in the NYC area is less than optimal. Things got better when I took it on a trip to San Francisco, which makes sense since the Bay area is Apple's home base. In SF, voice quality was decent, and I didn't drop any calls. Handsfree tethering to two cars (an Acura and a BMW) were the best of any phone I've used, even compared to the Moto RAZR v3. EDGE 2.5G Internet access was OK in NYC, and a little better in SF.

SF has a big plus with the MUNI and BART mobile web sites. It was neat checking on the timing of the next BART train or Muni bus while waiting at a stop. I wish they could do something like that in my home base of NYC. I couldn't tether the iPhone to my notebook like I can with the MDA, but that's OK, since Safari is the best mobile phone browser I've used yet.

Lack of Flash and Java are the notable minuses for mobile Safari. I was still able to access my office's webmail, many information sites, and a couple of iPhone-optimized sites as well. Calendar and contact functions were as good as any non-smartphone, and synced to Entourage/Outlook, so I was happy there.

As a media player, the iPhone was almost perfect. I say almost, because of that darned recessed headphone jack. I kludged a rough 3-inch headphone extension cable from a headphone extender I got in a dongle for a pair of wireless headphones. This was a usable if awkward solution. Like my colleagues Sascha Segan and Tim Gideon, I enjoyed using the touchscreen interface, and movies looked great on the iPhone's bright semi-wide screen. The one other major nit I could pick about the iPhone is that it is awkward to use in your pocket: there is no tactile feedback like on the nanos' clickwheel, so you can't FF to the next song if your shuffle play picks the wrong song for your current mood. This would be moot if the iPod wired FM remote worked with the iPhone or iPod Touch, but sadly that's not the case.

So overall: iPhone as a Phone (3.5 out of 5), Internet Tablet (3.5 out of 5), native apps (1.5 out of 5, there are none aside from a couple of built in widgets), PDA (4 out of 5), and media player (4.5 out of 5).

The iPod touch is the so-called "iPhone without the phone", and the interface issues are similar to the iPhone. The iPod Touch deletes the iPhone's physical volume controls and speakers, so annoyingly everything on the Touch is done on the touchscreen. It is a brilliant media player, though I wish the speakers were still there for viewing video podcasts and TV shows. Thank goodness the Touch works without a headphone adapter. The iPod Touch also deletes calendar entry, but that's OK, since I use my PDAs to check meetings, not schedule them, Safari is still here, but is limited to WiFi Hotspots. This is the biggest drawback for me, since I like to check things like transit delays on my MDA daily. Having 16GB instead of the 8GB on the iPhone and nano is a nice perk, but not enough for me to shell out $399 for it. If the Touch had a Bluetooth Dial Up Networking profile, I would get that and a 3G Verzion phone with Bluetooth tethering. That would be sweet. (The Nokia N800 internet tablet with a 3G phone is a passable alternative, but unfortunately there aren't enough native apps, and besides, I bought too many iTunes tracks and videos to abandon iPod completely at this point).

iPod Touch rates: Phone (0 out of 5), Internet Tablet (3.0 out of 5), native apps (1 out of 5, just You Tube), PDA (3 out of 5), and media player (4.5 out of 5).

I didn't try out the 80GB and 160GB iPod Classic, because I simply don't need to carry my entire video and music library with me at all times. Also I tend to listen my playlists on shuffle, and hard drive players like the Classics are slower to react than flash players like the nanos and the iPhone/iPod Touch. Besides, the nano 3G and the classic share the same interface.

The iPod nano 3G is an upgrade to my current nano 2G. Apple added video, and changed the shape slightly. They also lowered the price to $199 for 8GB, which is great considering the functionality of the nano 3G. The video quality is excellent, even with such a small screen, though it is better suited to video podcasts and TV shows than full length movies in widescreen. While it has even less calendar and contact functionality than the Touch, this is OK, since the nano would (still) be a companion to my MDA rather than a replacement. Shuffle play on the nano is as good as on previous nanos, which is to say it is excellent. The drawbacks of the Touch aren't present on the nano, because it's more of a shrunk iPod Classic than an iPhone with no Phone.

iPod nano scores: Phone (0 out of 5), Internet Tablet (0 out of 5), native Apps (3 out of 5, games and a few 'extras'), PDA (2 out of 5), media player (5 out of 5).

So who won? Well since the iPhone doesn't have Flash, a usable headphone jack, or 3G or faster data (yet), it is a "wait for version 2.0" situation for me. As it stands right now, the first iPhone isn't quite enough for me to leave T-mobile for AT&T wireless. A 3G data, 16GB iPhone with AT&T (or Verizon) would be enough for me to leave my MDA in the drawer of obsolete tech forever.

The iPod Touch is a really nice media player, but I would have to still carry the MDA for everything else, and that's two bulky devices to carry. Maybe if they included tethering or at least the physical volume controls and the speakers. The choice (if I made it today) is upgrading to the nano 3G, and continuing to use the MDA for phone, mobile Internet, apps, and PDA. The nano is still small enough to ignore in a pocket, and with the video playback, it gets me all the new podcasts and shows I've discovered on this journey. It's also half the price of the iPhone or 16GB Touch, so it's a no-brainer.

The Winnah!